Isolation and structure determination of the first example of the azeto[2,3-c]quinolizinedione ring system
journal contributionposted on 11.09.2015, 10:51 by Beatriz Fernandez-Diaz-Ropero, Mark Elsegood, Gary Fairley, Gareth Pritchard, Simon J. Teat, George Weaver
An unexpected azeto[2,3-c]quinolizinedione has been isolated during synthetic studies on the base catalyzed condensation of ethyl 6-methylpyridin-2(1H)-on-1-ylacetate with benzil. Closure of a fused four-membered azetidinone ring occurred when potassium hexamethyldisilazide was employed as the base. The structure of the product was confirmed by synchrotron X-ray crystallography. A possible mechanism for the formation of the product is considered.
The authors thank AstraZeneca and Loughborough University for providing funding.